US2443136A - Photographic elements containing 1, 3, 4-triazaindolizine cyanine dyes - Google Patents
Photographic elements containing 1, 3, 4-triazaindolizine cyanine dyes Download PDFInfo
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- US2443136A US2443136A US661353A US66135346A US2443136A US 2443136 A US2443136 A US 2443136A US 661353 A US661353 A US 661353A US 66135346 A US66135346 A US 66135346A US 2443136 A US2443136 A US 2443136A
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- US
- United States
- Prior art keywords
- ethiodide
- triazaindolizine
- dye
- grams
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 239000000975 dye Substances 0.000 title description 33
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 title description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- 239000000839 emulsion Substances 0.000 description 19
- -1 selenazoles Chemical class 0.000 description 19
- 150000003839 salts Chemical class 0.000 description 15
- 125000000217 alkyl group Chemical group 0.000 description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 235000019441 ethanol Nutrition 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- 125000003710 aryl alkyl group Chemical group 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 150000002431 hydrogen Chemical group 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- ZUNKMNLKJXRCDM-UHFFFAOYSA-N silver bromoiodide Chemical compound [Ag].IBr ZUNKMNLKJXRCDM-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 229920002301 cellulose acetate Polymers 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- MUDSDYNRBDKLGK-UHFFFAOYSA-N 4-methylquinoline Chemical compound C1=CC=C2C(C)=CC=NC2=C1 MUDSDYNRBDKLGK-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- WMUIZUWOEIQJEH-UHFFFAOYSA-N benzo[e][1,3]benzoxazole Chemical compound C1=CC=C2C(N=CO3)=C3C=CC2=C1 WMUIZUWOEIQJEH-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 230000002165 photosensitisation Effects 0.000 description 2
- 239000003504 photosensitizing agent Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- YKYIFUROKBDHCY-ONEGZZNKSA-N (e)-4-ethoxy-1,1,1-trifluorobut-3-en-2-one Chemical group CCO\C=C\C(=O)C(F)(F)F YKYIFUROKBDHCY-ONEGZZNKSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- AIGNCQCMONAWOL-UHFFFAOYSA-N 1,3-benzoselenazole Chemical compound C1=CC=C2[se]C=NC2=C1 AIGNCQCMONAWOL-UHFFFAOYSA-N 0.000 description 1
- ODIRBFFBCSTPTO-UHFFFAOYSA-N 1,3-selenazole Chemical compound C1=C[se]C=N1 ODIRBFFBCSTPTO-UHFFFAOYSA-N 0.000 description 1
- OIWIYLWZIIJNHU-UHFFFAOYSA-N 1-sulfanylpyrazole Chemical compound SN1C=CC=N1 OIWIYLWZIIJNHU-UHFFFAOYSA-N 0.000 description 1
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 1
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 1
- FECNOIODIVNEKI-UHFFFAOYSA-N 2-[(2-aminobenzoyl)amino]benzoic acid Chemical class NC1=CC=CC=C1C(=O)NC1=CC=CC=C1C(O)=O FECNOIODIVNEKI-UHFFFAOYSA-N 0.000 description 1
- AVPSAOBJPPJHCY-UHFFFAOYSA-N 2-methylsulfanyl-1,3-benzoselenazole Chemical compound C1=CC=C2[se]C(SC)=NC2=C1 AVPSAOBJPPJHCY-UHFFFAOYSA-N 0.000 description 1
- CBXAWZGFEDZKFR-UHFFFAOYSA-N 2-methylsulfanyl-1,3-benzoxazole Chemical compound C1=CC=C2OC(SC)=NC2=C1 CBXAWZGFEDZKFR-UHFFFAOYSA-N 0.000 description 1
- QFGRBBWYHIYNIB-UHFFFAOYSA-N 2-methylsulfanyl-4,5-dihydro-1,3-thiazole Chemical compound CSC1=NCCS1 QFGRBBWYHIYNIB-UHFFFAOYSA-N 0.000 description 1
- NCJSBVUUUHBCQS-UHFFFAOYSA-N 2-methylsulfanylbenzo[e][1,3]benzothiazole Chemical compound C1=CC=C2C(N=C(S3)SC)=C3C=CC2=C1 NCJSBVUUUHBCQS-UHFFFAOYSA-N 0.000 description 1
- HPYQPLGUSVCKSX-UHFFFAOYSA-N 2-methylsulfanylbenzo[e][1,3]benzoxazole Chemical compound C1=CC=C2C(N=C(O3)SC)=C3C=CC2=C1 HPYQPLGUSVCKSX-UHFFFAOYSA-N 0.000 description 1
- NINCMKJQHKDMPH-UHFFFAOYSA-N 2-methylsulfanylquinoline Chemical compound C1=CC=CC2=NC(SC)=CC=C21 NINCMKJQHKDMPH-UHFFFAOYSA-N 0.000 description 1
- UTBVIMLZIRIFFR-UHFFFAOYSA-N 2-methylthio-1,3-benzothiazole Chemical compound C1=CC=C2SC(SC)=NC2=C1 UTBVIMLZIRIFFR-UHFFFAOYSA-N 0.000 description 1
- CASOXVQOUDGNOW-UHFFFAOYSA-N 2-phenylsulfanyl-1,3-benzothiazole Chemical compound N=1C2=CC=CC=C2SC=1SC1=CC=CC=C1 CASOXVQOUDGNOW-UHFFFAOYSA-N 0.000 description 1
- GSCAIFIGUGOYGC-UHFFFAOYSA-N 2-phenylsulfanyl-4,5-dihydro-1,3-thiazole Chemical compound S1CCN=C1SC1=CC=CC=C1 GSCAIFIGUGOYGC-UHFFFAOYSA-N 0.000 description 1
- MVVFUAACPKXXKJ-UHFFFAOYSA-N 4,5-dihydro-1,3-selenazole Chemical compound C1CN=C[Se]1 MVVFUAACPKXXKJ-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 1
- YDQJXVYGARVLRT-UHFFFAOYSA-N Lepidine Natural products C=1C=CC(CC=2NC=CN=2)=CC=1OC=1C(OC)=CC=CC=1CC1=NC=CN1 YDQJXVYGARVLRT-UHFFFAOYSA-N 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 101150057833 THEG gene Proteins 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 description 1
- 239000011354 acetal resin Substances 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- AMTXUWGBSGZXCJ-UHFFFAOYSA-N benzo[e][1,3]benzoselenazole Chemical compound C1=CC=C2C(N=C[se]3)=C3C=CC2=C1 AMTXUWGBSGZXCJ-UHFFFAOYSA-N 0.000 description 1
- KXNQKOAQSGJCQU-UHFFFAOYSA-N benzo[e][1,3]benzothiazole Chemical compound C1=CC=C2C(N=CS3)=C3C=CC2=C1 KXNQKOAQSGJCQU-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 125000005805 dimethoxy phenyl group Chemical group 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- DZVCFNFOPIZQKX-LTHRDKTGSA-M merocyanine Chemical compound [Na+].O=C1N(CCCC)C(=O)N(CCCC)C(=O)C1=C\C=C\C=C/1N(CCCS([O-])(=O)=O)C2=CC=CC=C2O\1 DZVCFNFOPIZQKX-LTHRDKTGSA-M 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000002916 oxazoles Chemical class 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- DSNYFFJTZPIKFZ-UHFFFAOYSA-N propoxybenzene Chemical group CCCOC1=CC=CC=C1 DSNYFFJTZPIKFZ-UHFFFAOYSA-N 0.000 description 1
- SMUQFGGVLNAIOZ-UHFFFAOYSA-N quinaldine Chemical class C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/76—Photosensitive materials characterised by the base or auxiliary layers
- G03C1/825—Photosensitive materials characterised by the base or auxiliary layers characterised by antireflection means or visible-light filtering means, e.g. antihalation
- G03C1/83—Organic dyestuffs therefor
- G03C1/832—Methine or polymethine dyes
Definitions
- the residual dye stain is particularly undesirablein photographic films and papers. Moreover, it may frequently be desirable to use such dyes as screening or filter'layers, in which case lar centrations of the dyes are necessary. Such applications are often limited by the difficulty of removal of dyestufl from the layer during the processing operations because of low water' solubility.
- a further object is to provide such dyes which are added to photographic silver-halide emul-r sions or coated thereon as an overcoating whereby the sensitivity of the emulsion is increased.
- a still further object istoprovide photo-sensitizing dyestufis having appreciable water solubility and readily removed from the exposed emulsion layer during processing.
- R1 represents an alkyl group, e. g., methyl or ethyl
- R2 represents hydrogen, alkyl, e. g., methyl, ethyl; propyl; butyl, and the like, carbalkox-y, e. g., carbmethoxy, carbethoxy, carbpropoxy and the, like, aryl, e.
- R3 and R4 represent hydrogen, alkyl and aryl as in R2, aralkyL.e;g.,.benzylqmethylsbenzyl, ethyl benzyl, etc., alkoxyph'enyl, e. g., methoxyphenyl, ethoxyphenyl, propoxyphenyl and the like, dialkoxyphenyl, e. g.,, dimethoxyphenyl, diethoxyphenyl, dipropoxyphenyl; and the like.
- the compounds numbered from 1 to 6, 9 to 14, and 16 to 22 areprepared by heating a 3-amino- 1,2,4-triazole with an, appropriate B-diketone in absolute alcohol in the presence of a small quantity of an organic' -base such' as triethylamine or piperidine.
- an organic' -base such' as triethylamine or piperidine.
- Compounds numbered 7, 8 and 15 are preparedby. heating the same triazole with ethyl ethoxymethylene-a-cetoacetate in glacial aceticacid.
- CH C 5-methyl-7-phenyl-l,3,4-triazaindolizine 5,7-dimethyl-2 ⁇ 2-methoxyplienyl]1,3,4-triazaindolizine i /CH 5-,methyl-7-[4-methoxyphenyl]-l-,3,4-triazaindolizine (20) O 0 Ha OCH:
- the dyestuffs derived from the alkyl or aralkyl quaternary salts of 1,3,4-triazaindolizines and cyclammonium quaternary cyanine dye salt intermediates have the following general forwherein R is a hydrocarbon grou 3.01 am le, alkyl group, e. g. methyl, ethyl, propyl, butyl, amyl, and the like, or aralkyl group, e. g., benzyl, phenethyl, and the like, R2, R3 and R4 have the same Values as given above, R5 is either hydrogen, alkyl, e.
- Re is either hydrogen, or a methyl group
- X represents an anionic acid radical, e. g., Cl, Br, I, C104, SO4CH3, SO4C2H5, SO3C6H4CH3 and the like
- Z represents the atoms necessary to complete a.
- nitrogenous heterocyclic system ofthe type usual in cyanine dyes such as pyridine, lepidine, quinol-ine, indoline, oxazole, thiaz'oline, thiazole, thiodiazole, selenazole, selenazoline, oxazoline, benzothiazole, benzoselenazole, benzoxazole, naphthothiazole, naphthoselenazole, and the like, and n represents a positive integer ran ing from 1 to 2.
- MONOMETHINE As examples of suitable cyclammon'ium quaternary cyanine dye salt intermediates, having a, reactive group in 2-p0siti0n to the nitrogen atom thereof, the following may be mentioned:
- 1,3,4-triazainodolizine bases are converted are their corresponding alkyl or aralkyl quaternary cyclammonium salts in the manner usual fo'r' the conversion of other nitrogenous h eterocyclic.bases to the quaternary salt form, i. e., by fusion with an alkyl or aralkyl halide, or by heating the base.
- the amount of condensing agent used mayvary-within'wide limits, e; g" Concentrations ranging from 1 mol to about 1'5 mols are preferred, however. 7
- EXAMPLE III t about V 3.65 grams of: 5 methy1-7-pheny1-1,3,4-triazae indolizine ethiodide and 3.04 grams of 2-p-a cet anilidovinyl benzothiazole ethiodide are refluxed in 15 cc, of dr pyridine for 40 minutes. Ethyl alcohol is added to the cooled-reaction mixture and after several hours of standing, the dye "crystals are filtered and recryst'alliz ed from ethanoL;
- EXAMPLE IV 0.45 gram of 5-methy1-7-pheny1-1,3,4-triazaindolizine ethiodide, 0.39 gram of Z-(B-ethyl-B- methylmercaptovinyl) -6-methoxy benzothia'z'ole ethi-odide, 15 cc. of isopropyl alcohol and. 0.2 cc. of triethylamine are refluxed for one hour. 1 Upon cooling, the dye precipitates. The product is filtered and recrystallized from ethanol.
- EXAMPLE VIII crystals are filtered and recrystallized from etha-.
- Example VIII was repeated with the exception that 3.30 grams of 5,7-diethyl-1,3,4-triazaindolizine ethiodide was substituted for 3.17 grams of 2,5,7-trimethy1-1,3,4-triazaindolizine ethiodide.
- photographic gelatinosilver-developing-out emulsions such as gelatinosilver-chloride, gelatino-silver chlorobromide, gelatino-silver-bromoiodide emulsions, and the like, containing the monoand polymethine dyestuffs of the present invention, it is only necessary to disperse the dyestuffs in the emulsions. It is convenient to add the compounds from solutions in appropriate solvents. An alcohol, such as methanol or ethanol, is satisfactory as a solvent for the dyestuffs.
- Emulsions prepared in accordance with this invention can be coated in the usual manner upon any desired support, such as cellulose nitrate, cellulose acetate, polyvinyl acetal resin, glass, paper and the like.
- the concentration of these new dyestufis in the emulsion can vary widely, i. e., from about 5 to about 100 mg. per liter of flowable emulsions.
- the concentration of. the dyestuff will vary'according to the type of light-sensitive material in the emulsion and according to the effect desired.
- the suitable and most economical concentration for any given emulsion will be apparent to those skilled in the art upon making the ordinary tests and observations customarily used in the art of emulsion making. r g
- the new dyestuffs of the present invention have an additional advantage in that they can be employed in th manufacture of light filters, antihalation coatings and in the coloring of cellulose acetate yarn, i. e., cellulose acetate silk. This is due primarily'to the increased water solubility imparted to the dyestuffs by the presence therein of the 1,3,4-triazaindolizine nucleus.
- R represents a member selected from the class consisting of alkyl and aralkyl groups
- R2 is a member selected from the class consistingof. hydrogen, alkyl, carbalkoxy, and aryl groups
- Ea and R4 represent the members'selectecl from theg class consisting of hydrogen, alkyl, aryl, aralkylg; alkoxyphenyl, and dialkoxyphenyl groups
- R5 is a member selected from the class consisting of hydrogen and alkyl groups
- Re is a meniber se lected from the class consisting of hydrogen and methyl group
- nv represents a positive integer ranging from 1 to 2
- X represents an anionic radical
- Z represents the atoms necessary to complete a heterocyclic nitrogenous systemof the type:
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE472445D BE472445A (en, 2012) | 1946-04-11 | ||
| US661353A US2443136A (en) | 1946-04-11 | 1946-04-11 | Photographic elements containing 1, 3, 4-triazaindolizine cyanine dyes |
| US675289A US2439210A (en) | 1946-04-11 | 1946-06-07 | Photographic silver-halide emulsions containing 1,3,4-triazaindolizine cyanine dyes |
| GB4196/47A GB632808A (en) | 1946-04-11 | 1947-02-13 | Cyanine dyes derived from 1, 3, 4-triazaindolizines and photographic silver halide emulsions sensitized therewith |
| FR944129D FR944129A (fr) | 1946-04-11 | 1947-03-28 | Nouvelles matières colorantes cyanines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US661353A US2443136A (en) | 1946-04-11 | 1946-04-11 | Photographic elements containing 1, 3, 4-triazaindolizine cyanine dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2443136A true US2443136A (en) | 1948-06-08 |
Family
ID=24653237
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US661353A Expired - Lifetime US2443136A (en) | 1946-04-11 | 1946-04-11 | Photographic elements containing 1, 3, 4-triazaindolizine cyanine dyes |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US2443136A (en, 2012) |
| BE (1) | BE472445A (en, 2012) |
| FR (1) | FR944129A (en, 2012) |
| GB (1) | GB632808A (en, 2012) |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2689849A (en) * | 1952-09-10 | 1954-09-21 | Eastman Kodak Co | Cyanine dyes containing the triazolo[4, 3-alpha] quinoline or tetrazolo[alpha] quinoline nucleus |
| US2693472A (en) * | 1950-03-20 | 1954-11-02 | Ilford Ltd | Polymethine compounds |
| US2887480A (en) * | 1956-08-30 | 1959-05-19 | Eastman Kodak Co | Cyanine bases containing an azaindenyl nucleus |
| US4209621A (en) * | 1979-04-27 | 1980-06-24 | American Cyanamid Company | (Substituted-phenyl)-1,2,4-triazolo[4,3-a]-pyrimidines and (substituted-phenyl)-1,2,4-triazolo[1,5-a]pyrimidines |
| US5294709A (en) * | 1989-02-28 | 1994-03-15 | Fuji Photo Film Co., Ltd. | Methine compounds and methine dyes |
| US6020338A (en) * | 1998-02-11 | 2000-02-01 | American Cyanamid Company | Fungicidal 7-alkyl-triazolopyrimidines |
| US20050090665A1 (en) * | 2001-07-05 | 2005-04-28 | Bernd Muller | Fungicidal triazolopyrimidines, method for the production thereof and use thereof in controlling noxious fungi and agents containing said compounds |
| US20060217400A1 (en) * | 2002-12-20 | 2006-09-28 | Mueller Bernd | Triazolopyrimidines, methods for the production thereof, use thereof for controlling harmful fungi, and substances containing said triazolopyrimidines |
| WO2007116011A3 (de) * | 2006-04-10 | 2007-12-21 | Basf Ag | Substituierte triazolopyrimidine, verfahren zu ihrer herstellung und ihre verwendung zur bekämpfung von schadpilzen sowie sie enthaltende mittel |
| WO2010018868A1 (ja) * | 2008-08-14 | 2010-02-18 | 石原産業株式会社 | トリアゾロピリミジン誘導体又はその塩を含有する有害生物防除剤 |
| CN109180684A (zh) * | 2018-09-28 | 2019-01-11 | 郑州大学 | 一种双芳基类化合物及其制备方法 |
| US11814734B2 (en) | 2019-05-13 | 2023-11-14 | Ecolab Usa Inc. | 1,2,4-triazolo[1,5-a] pyrimidine derivative as copper corrosion inhibitor |
-
0
- BE BE472445D patent/BE472445A/xx unknown
-
1946
- 1946-04-11 US US661353A patent/US2443136A/en not_active Expired - Lifetime
-
1947
- 1947-02-13 GB GB4196/47A patent/GB632808A/en not_active Expired
- 1947-03-28 FR FR944129D patent/FR944129A/fr not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2693472A (en) * | 1950-03-20 | 1954-11-02 | Ilford Ltd | Polymethine compounds |
| US2689849A (en) * | 1952-09-10 | 1954-09-21 | Eastman Kodak Co | Cyanine dyes containing the triazolo[4, 3-alpha] quinoline or tetrazolo[alpha] quinoline nucleus |
| US2887480A (en) * | 1956-08-30 | 1959-05-19 | Eastman Kodak Co | Cyanine bases containing an azaindenyl nucleus |
| US4209621A (en) * | 1979-04-27 | 1980-06-24 | American Cyanamid Company | (Substituted-phenyl)-1,2,4-triazolo[4,3-a]-pyrimidines and (substituted-phenyl)-1,2,4-triazolo[1,5-a]pyrimidines |
| US5294709A (en) * | 1989-02-28 | 1994-03-15 | Fuji Photo Film Co., Ltd. | Methine compounds and methine dyes |
| US6020338A (en) * | 1998-02-11 | 2000-02-01 | American Cyanamid Company | Fungicidal 7-alkyl-triazolopyrimidines |
| US20050090665A1 (en) * | 2001-07-05 | 2005-04-28 | Bernd Muller | Fungicidal triazolopyrimidines, method for the production thereof and use thereof in controlling noxious fungi and agents containing said compounds |
| US7300908B2 (en) * | 2001-07-05 | 2007-11-27 | Basf Aktiengesellschaft | Fungicidal triazolopyrimidines, method for the production thereof and use thereof in controlling noxious fungi and agents containing said compounds |
| US20060217400A1 (en) * | 2002-12-20 | 2006-09-28 | Mueller Bernd | Triazolopyrimidines, methods for the production thereof, use thereof for controlling harmful fungi, and substances containing said triazolopyrimidines |
| WO2007116011A3 (de) * | 2006-04-10 | 2007-12-21 | Basf Ag | Substituierte triazolopyrimidine, verfahren zu ihrer herstellung und ihre verwendung zur bekämpfung von schadpilzen sowie sie enthaltende mittel |
| WO2010018868A1 (ja) * | 2008-08-14 | 2010-02-18 | 石原産業株式会社 | トリアゾロピリミジン誘導体又はその塩を含有する有害生物防除剤 |
| CN109180684A (zh) * | 2018-09-28 | 2019-01-11 | 郑州大学 | 一种双芳基类化合物及其制备方法 |
| US11814734B2 (en) | 2019-05-13 | 2023-11-14 | Ecolab Usa Inc. | 1,2,4-triazolo[1,5-a] pyrimidine derivative as copper corrosion inhibitor |
Also Published As
| Publication number | Publication date |
|---|---|
| FR944129A (fr) | 1949-03-28 |
| BE472445A (en, 2012) | |
| GB632808A (en) | 1949-12-05 |
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